Although the two clubs have frequently been in the same division as each other since 1919, the rivalry has largely arisen since around 1990. Many of the clashes in recent times between the two teams in the late 1990s and early 2000s have been due to the teams being fierce rivals for the Premier League and FA Cup.

In recent years with Arsenal being less competitive, the rivalry has diminished somewhat according to former Arsenal player Lee Dixon, while Sir Alex Ferguson has also stated that the two teams have cooled from those previously "heated" exchanges.[1][5]

A particularly memorable match between the two sides came on 1 February 1958, when they met in a league fixture at Highbury – the last league game that United played before the Munich air disaster five days later, which claimed the lives of eight of their players and saw two other players injured to such an extent that they never played again. United won the game 5–4, with goals from Tommy Taylor (twice), Duncan Edwards, Bobby Charlton and Dennis Viollet. Five of the United players who would lose their lives as a result of crash took to the field in the game – captain and full-back Roger Byrne, right-half Eddie Colman, centre-half Mark Jones, left-half Duncan Edwards and centre-forward Tommy Taylor.

Another high profile clash came more than 20 years later, in the final of the FA Cup on 12 May 1979. A 100,000-strong crowd saw Arsenal take a 2–0 lead in the first half thanks to goals from Brian Talbot and Frank Stapleton, and with just five minutes left on the clock their lead was still intact. Then, in the 86th minute, Gordon McQueen pulled a goal back for United, and two minutes later they equalised with a goal from Sammy McIlroy. However, barely a minute after United equalised, Arsenal's Alan Sunderland scored an 89th minute goal to win the cup 3–2 for Arsenal.

Although the two clubs had previously contested many important matches, such as the 1979 FA Cup Final, the rivalry is generally perceived to have begun with a notorious match at Old Trafford on 20 October 1990, which resulted in both clubs being docked points in the 1990–91 First Division. Alex Ferguson has stated that he believes that the rivalry predates this by a few years, however, to a match in January 1987 when David Rocastle was sent off for retaliating against a foul by Norman Whiteside.[6]

On 19 August 1989, at the beginning of Alex Ferguson's fourth season as Manchester United manager (and with the club still yet to win any silverware under his management), defending league champions Arsenal travelled to Old Trafford for the first league game of the season. United won 4–1 with goals from Steve Bruce, Mark Hughes, Brian McClair and new signing Neil Webb, with Arsenal's consolation goal being scored by David Rocastle. Arsenal finished the season fourth in First Division with 62 points, putting them 17 points adrift of champions Liverpool. Although United had a disappointing season in the league, finishing 13th (five points and five places clear of the relegation zone), they ended the season as winners of the FA Cup.

In 1990–91, Arsenal won the second of their league titles under the management of George Graham, losing just one of their 38 league games all season. They sealed their title on 6 May 1991, just before the kick-off in their league game against United at Highbury, which they went on to win 3–1. Their title was confirmed without kicking a ball as their last remaining challengers Liverpool had been defeated by Nottingham Forest earlier in the day. The season had already seen two high profile clashes between United and Arsenal – one being the ill-tempered league clash at Old Trafford on 20 October, the other in the Football League Cup just over a month later. The two clubs were drawn to play at Highbury in the fourth round tie on 28 November 1990. United won the tie 6–2, with 19-year-old winger Lee Sharpe scoring a hat-trick.

After the arrival of Arsène Wenger in 1996, United and Arsenal became perennial rivals for the Premier League. In the first match at Highbury between the two sides after Wenger's arrival, an antipathy between Arsenal's Ian Wright and United's Peter Schmeichel came to a head with confrontations on the pitch and in the tunnel after the match.[7] In April 1997, Ferguson publicly commented on Wenger's views on United's fixture list by saying: "Wenger doesn't know anything about English football. He's at a big club – well, Arsenal used to be big. He should keep his mouth shut, firmly shut. He's a novice and should keep his opinions to Japanese football."[8]

United had won four of the first five editions of the newly branded league, before Arsenal won the league and cupdouble in Wenger's first full season in charge. The following season saw United win the treble, beating Arsenal by one point in the Premier League and in the semi-finals of the FA Cup. United followed this up with back-to-back Premier League wins in 1999–2000 and 2000–01, to become the first team to win three consecutive Premier League titles. Arsenal won a double for the second time under Wenger in 2001–02, securing the league title by beating United 1–0 at Old Trafford.[9] United again won the title back in 2002–03, where a late season encounter between the teams ended in controversial circumstances after Sol Campbell was sent off for an elbow on Ole Gunnar Solskjær.[10]

Another key point in this rivalry was during the 2003–04 Premier League season. During this year, Arsenal went on to win the league with an unbeaten record. They were labeled as "The Invincibles" and during their first game with Manchester United, they drew 0–0 at Old Trafford in a match dubbed the "Battle of Old Trafford". Arsenal captain Patrick Vieira was sent off in the 80th minute for two bookable offences and in second half stoppage time, Gunners defender Martin Keown brought down United's Diego Forlán in the Arsenal penalty area, Ruud van Nistelrooy stepped up for the spot kick but his shot rebounded off the crossbar. This was followed by scenes of jubilation from the Arsenal players, especially Martin Keown who confronted Van Nistelrooy after his miss. The resulting scuffle led to another fracas after the final whistle, which ended up with four players from both sides being given yellow cards.

The next game between these two clubs was held at Highbury, which resulted in a 1–1 draw. At the end of the season, Arsenal ended with 90 points while Manchester United finished with 75 points in the third position. Even famous arguments and fights occurred between players, such as Patrick Vieira and Roy Keane. Arsenal went on to hold a national record of 49 league games unbeaten, which was ended by a controversial 2–0 defeat at Old Trafford after Wayne Rooney was adjudged to have been fouled in the area by Arsenal defender Campbell. This game was later called "Battle of the Buffet". The clubs met again five weeks later in the 2004–05 Football League Cup quarter-finals at Old Trafford and even though both sides fielded weakened teams, the match was nothing short of drama. David Bellion gave United the lead in just 19 seconds, but tempers began to flare in the second half; a late tackle by Robin van Persie on Kieran Richardson resulted in a fracas between both sets of players, which concluded with both protagonists getting booked by referee Mark Halsey. The game finished 1–0.[11] In the reverse league fixture, Keane and Vieira had to be separated in the tunnel before the match by referee Graham Poll. Vieira gave Arsenal the lead in the eighth minute of the match but United ran out 4–2 winners.[12]

The 2005 FA Cup Final, between the two sides, was the first time in the competition's history that the final was decided on a penalty shoot-out. Arsenal beat United 5–4, following a goalless draw after extra time.[13] Arsenal forward José Antonio Reyes became the second player in Cup Final history to be sent off, following his second yellow card near the end of extra time.

With Chelsea's back-to-back Premiership titles in 2004–05 and 2005–06 under José Mourinho, the United-Arsenal rivalry has cooled somewhat. United manager Alex Ferguson was heard remarking before the 6 May 2007 game between Arsenal and Chelsea that he was rooting for "The Gunners", a game where Arsenal held Chelsea to a draw which clinched the title for United.[1][2] The teams met in the semi-finals of the 2008–09 UEFA Champions League with United winning 4–1 on aggregate.

In December 2010, United manager Alex Ferguson made a personal plea to the United fans to no longer sing a "sick" chant at Arsenal manager Arsène Wenger, as those kind of chants from fans were considered an embarrassment to Manchester United.[14] With both teams going for the Premier League title in May 2011, Arsenal won their first game against Manchester United since November 2008, to leave United just three points ahead of Chelsea and six ahead of Arsenal going into the final three games of the season. Nevertheless, United won the league, nine points ahead of Chelsea and twelve points ahead of Arsenal.

In August 2012, Arsenal captain Robin van Persie was transferred to Manchester United after stating that he would not renew his contract with Arsenal. It was speculated that he would move to a club overseas, but signed for Manchester United, the first Arsenal player to do so since Viv Anderson in 1987.[17]

Sir Alex Ferguson's relationship with Arsène Wenger turned cordial in later years.

It was not until Wenger’s arrival in October 1996 that Arsenal remerged as a serious league competitor. By the end of the 1996–97 season, Manchester United amassed their fourth title in five seasons, whereas Arsenal finished the campaign in third – their highest position since the formation of the Premier League in 1992. During the season, Wenger commented on rule changes which permitted an extension to the league calendar: "It's wrong the programme is extended so Manchester United can rest and win everything."[18] His observation irked Ferguson, who replied: “He has no experience of English football. He has come here from Japan, and now he is telling everyone how to organise our football. Unless you have been in the situation and had the experience then he should keep his mouth shut, firmly shut.”

The relationship between both managers was evidently hostile to begin with. Ferguson noted that Wenger was the only manager he came across in the league not to share a drink with after matches – an English football “tradition”.[19] In a joint interview with The Times and Daily Mail in 2009, Wenger said his discourtesy was mistaken for mistrust and managers “cannot be completely friendly and open up." When asked if this was the reason he avoided the post-match drink, he replied: "Most of the time, yes. What can you say if you have won? And if you have lost all you want to do is get home and prepare for the next game."[20]

In January 2005, Ferguson and Wenger were embroiled in a new row over what had happened in the tunnel after "Pizzagate". Ferguson alleged that Wenger called his players "cheats" and never apologised for his team's behaviour: "It's a disgrace, but I don't expect Wenger to ever apologise, he's that type of person." Wenger then claimed Ferguson was guilty of bringing the game into disrepute; he told reporters that he "will never answer any questions any more about this man," but went further to question the motive of the press: "What I don't understand is that he does what he wants and you are all at his feet." Both managers came under pressure from the police, then Sports Minister Richard Caborn and Premier League chairman Richard Scudamore to put an end to the bickering.[21] Ferguson and Wenger agreed to tone down their words, in an attempt to defuse the rivalry. In later years, Ferguson said Arsenal's defeat “scrambled Arsène’s brain” and caused their relationship to breakdown for almost five years.[22]

"We both want to win and neither of us hides from having a go at each other."

The two managers have "exchanged some of football's best and bitterest verbal swipes."[24] In 1997, Ferguson described Wenger as a “novice” for complaining about the fixture programme and said of his linguistic skills: “They say he’s an intelligent man, right? Speaks five languages! I’ve got a 15-year-old boy from the Ivory Coast who speaks five languages!” After Arsenal's defeat to Manchester United in February 1997 – a match marred by a bust up between Wright and Schmeichel, Wenger referred to Ferguson’s interference: "I was surprised to see Ferguson on the pitch because you can only play eleven.”[18] When Ferguson asserted that his team played the best football in England during the 2001–02 season, Wenger quipped: "Everyone thinks they have the prettiest wife at home," a subtle remark that Ferguson initially suspected was a taunt at his own wife Cathy.[25]

Such was the media's fascination of both managers' insults towards one another, psychologists were brought in to read and contrast their personalities.[18] John Kramer, a sports psychologist suggested in 2004 that Ferguson and Wenger used their rivalry in order to relax before an important match. To him, Ferguson was "...the past master in terms of creating an environment of keeping his players hungry" by using a persecution complex; Wenger on the other hand diffuses the psychology and would rather "...tell his players they are all superb and will attempt to create an environment where they are able to show off their skills without the rest of it." Kramer concluded that both managers' comments "adds to the drama", but was insignificant in the games between the two clubs.[26]

Ferguson in his autobiography said a major turning point in his relationship with Wenger was after the Champions League semi-final of 2009; the Arsenal manager invited his competitor into the dressing room and congratulated him on United's win. Wenger himself noted that their relationship had become genial since his team stopped competing with Manchester United for major honours. The move to the Emirates Stadium in 2006 is often cited as the reason why, given it coincided with a transitional phase for the club. Several experienced first teamers were displaced in favour of youth and the style of football became shifted more towards ball retention.[27] Ferguson assessed the change in philosophy proved that Wenger did not "like to blend them too much with older players;" he also felt the team lacked a much needed balance between attack and defence.[28]